


Food For Thought

by SmartKIN



Series: So Damn Beautiful [2]
Category: Teen Wolf (TV)
Genre: Anxiety, Awkwardness, Crossdressing, Crossdressing Stiles Stilinski, M/M, Post Season 2, Pre-Slash
Language: English
Status: Completed
Published: 2014-07-28
Updated: 2014-07-28
Packaged: 2018-02-10 20:18:20
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,736
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2038716
Author URL: https://archiveofourown.org/users/SmartKIN/pseuds/SmartKIN
Summary: <blockquote class="userstuff">
              <p>Derek takes Stiles out. For milkshakes.</p>
            </blockquote>





	Food For Thought

**Author's Note:**

> This is now officially a series! I have tons of ideas already (and no time to write them xD), so stay tuned. Technically, this can be read as a stand alone, you don’t have to go back and read _I feel something so right_ if you don’t want to.  
>  To recap: This series explores cross-dressing as a life choice and not just as a kink (although there may be smexy times in later installments).
> 
> [BethBobby](http://ghostlywhitedirewolf.tumblr.com/) agreed to be my Beta once again and she was really great help (I'm always so insecure)! Thank you so much for doing this! <3

Summer holidays were officially halfway over and Stiles couldn’t help but contemplate killing himself with a rusty spork just to escape the utter boredom that came with having only one good friend to hang out with and who, unfortunately, had a job that occupied all of their time. In most circumstances, Stiles really tried to be a glass-half-full kind of guy, but not when it came to summer holidays. He wanted to smash the freaking glass until every last drop of its content had soaked into the semi-ugly carpet that he had found on one of his raids of the attic.

 

You could spend only so much time on tumblr and Wikipedia until your brains started to leak out of your ears.

 

He knew deep down that he should be thankful, because really, crippling boredom implied that _nothing interesting was currently happening_. And that included mysterious “animal attacks” and violent shoot-outs of the supernatural sort. But it also meant that Stiles had nothing to research and no reason to snoop around the Sheriff’s Department. Not that _that_ had ever stopped him before. It was just that lately he tried to be a good son. Well, better son. His dad really needed him to not get into trouble for as long as possible now that he had his job back.

 

Aaaaand that lead right back to the crux of the matter.

 

 _Boredom_.

 

Stiles glanced at his phone and tried to weigh the consequences of texting Lydia.

 

She had agreed to translate the bestiary and Stiles had been thrilled at first. Then he’d realized that Lydia was in no rush and _wouldn’t do it right away_. After the fifth text asking her how far along she was with the translation, she had promised to eviscerate him very slowly if he dared to text her again. Unless all of their lives were in danger. Or they decided to kill Peter Hale once and for all—a course of action he could get behind, if it weren’t for the fact that he still had nightmares from setting him on fire that one time.

 

To text her or not to text her, he thought, imitating a deep Shakespearean-sounding voice in his head.

 

He could make a list with pros and cons. Attempt a probability calculation. It would take some time until he could be absolutely sure texting Lydia wouldn’t work (unless you were a math genius, like Lydia—and he could hardly ask Lydia to calculate for him whether it would end badly if he texted her again). This way he would effectively kill a few hours of his _endless summer break_. Jesus.

 

He sighed and poked his phone listlessly. Lydia was probably lounging in the sun next to her swimming pool right now. With cocktails. And hunky men fanning her with palm leaves. Ugh.

 

Admitting defeat, Stiles rested his forehead on his desk.

 

Seriously, he thought, fuck his life.

 

He let out an emphatically long-drawn sigh.

 

Out of the blue, his phone vibrated with an incoming text.

 

His head shot up and he nearly fell off his chair accompanied by flailing arm movements in his haste to grab his phone. Once he’d steadied himself, he thumbed the screen to read the message, hoping Lydia had translated the damn bestiary on her own volition even if it was just to get him off her back.

 

When he saw who’d sent it, Stiles mouth went Sahara-dry in .3 seconds.

 

The text wasn’t from Lydia.

 

It was from Derek.

 

With his heartbeat suddenly thumping loudly in his chest, he read the two-word message. Well. Order.

 

**Get dressed.**

 

Stiles swallowed with difficulty. Like _dressed_ dressed?

 

He suddenly didn’t know whether he preferred prolonged boredom to whatever Derek was up to. He decided to make sure that Derek meant what Stiles thought he meant and quickly typed out a reply.

 

**Full attire takes time.**

 

The seconds it took for Derek to answer felt like an eternity to Stiles. His left leg bounced nervously against his will and he felt the unfathomable urge to bite his nails, which he had stopped doing sometime in middle school because he needed there to be enough of his nails left to paint in all colors of the rainbow.

 

His phone buzzed again and Stiles almost dropped it on the floor.

 

**You have two hours.**

 

Letting out a fluttering breath, he tried to calm down.

 

So this was happening.

 

He could do that. He could take a shower and shave his legs, find a nice dress, pick one of his wigs and paint his face. He could do that. Yeah.

 

Maybe.

 

His heart was in his throat and it took a while until he recognized the reason for his dizzying anxiety. It wasn’t that he was scared of other people seeing him all dolled up. He had a habit of spending days in San Francisco showing off this very private side of himself. Stiles had no problems walking down the street in a short, provokingly red dress and six-inch heels.

 

Why was he so freaking nervous?

 

It wasn’t like Derek hadn’t seen him in drag before. In fact, Derek was one of the very few people he personally knew who had seen him in drag. Which had been a weird-ass coincidence, running into him during one of his ‘outings’ like that.

 

It was just...

 

Usually he had time to plan his trips very carefully, making sure he had no prior engagements, that his friends were either busy or knew he wouldn’t have time for them. There was time to arrange his outfits, time to ease himself into it, time to breathe and relax. He had never had to do this on the fly, as it were.

 

Derek was stirring up his perfectly planned routine.

 

His heartbeat refused to slow down and he realized he needed to get a move on if he wanted to be ready when the friendly neighborhood alpha showed up at his door.

 

With trembling fingers, he grabbed fresh underwear from his drawer and headed into the bathroom. Locking the door, he quickly undressed and spend a moment just looking at himself in the mirror above the bathroom sink.

 

He knew what Derek was doing. He wasn’t stupid. The wolf was giving him the opportunity to step out of his comfort zone and be himself for a while.

 

Stiles hadn’t dressed in drag ever since running into Derek, which had nothing to do with _running into Derek_. He usually went months at a time without perfume and makeup. The daily routine of high school usually got in the way and he couldn’t be—be this person, be _himself_ where people who knew him would see. Only when things got bad, when he needed to breathe, did he manage to get out of town for a day or two.

 

Sometimes he fantasized about wearing skirts and dresses to school, like it was allowed, like it was normal. Or just going to the super market, or bringing his dad some lunch.

 

He didn’t even know whether people would actually give him shit for it. Beacon Hills had an active LGBT scene and nobody made fun of Danny at school (or anywhere else for that matter)—the town was a pretty tolerant place all things considered. But Stiles didn’t want to push his luck. It was still the United States of America and his dad was still the Sheriff. What if the people of this town weren’t happy that their Sheriff had a crossdressing son and refused to vote him back into office when the next elections rolled around?

 

He couldn’t do that to his dad, couldn’t do it to this family. They’ve had enough problems and didn’t need him to ruin his dad’s career. He’d almost managed that even without a questionable hemline showing off his frankly gorgeous legs (one of the things he actually liked about his appearance).

 

Stiles shook his head and stepped into the shower. No need to think about these things right now. He had a deadline and an impatient werewolf to worry about, who’d probably drag him out of the house in whatever state of undress he’d find himself in at the two-hour mark.

 

~

 

After a quick shower that consisted mostly of shaving his legs and armpits (and man, how did girls manage to have shaved legs _all the time?_ ) Stiles set up camp in the guestroom where he kept all of his ‘tools of the trade’. His own room was way too small to house two complete sets of wardrobe, as well as his wigs, his makeup, his shoes. His dad hadn’t minded when Stiles had taken over the guest room—nobody used it anyway. They never really had overnight guests who didn’t crash in Stiles’ room, which basically translated into no one but Scott tended to spend the night at the Stilinski residence.

 

Stiles bit his lower lip as he contemplated several outfits. It was impossibly hot outside, so that sort of eliminated all long-sleeved dresses. He stood in front of the wardrobe with a racing heart, staring at his clothes and feeling the seconds tick by. Where did Derek even intend to take him? Should he wear heels or flats? Some dresses looked weird on him without heels.

 

He was starting to feel a bit lightheaded at the sudden onset of panic. He needed to pick something stat or this would all go down the proverbial toilet. He knew he was starting to overthink this outing and that never helped to calm the perpetual low-level sensation of anxiety.

 

Before he could possibly resort to flipping a coin, he finally picked an airy summer dress that he knew looked good on him and some heels to complement its red and beige rose print. He got dressed and sat down in front of his mom’s old vanity, deliberately only thinking about colors of lipstick, eyeshadow and nail polish.

 

Taking deep, even breaths he told himself that he could do this. That he could just dress up like a girl and jump into Derek’s Camaro like this was a thing they did all the time.

 

~

 

Stiles sat in the kitchen literally watching paint dry—namely the nail polish he had applied very last minute, but which was thankfully one that dried super quickly—when he heard a honk from outside the house.

 

Wow, way to act like a complete douchebag, Derek.

 

Grabbing his purse from the kitchen table, he quickly slipped into his heels, almost tripping over his own two feet.

 

“Shit,” he cursed under his breath. “Get it together!”

 

He tripped toward the front door, briefly stopping to examine himself one more time in the mirror to make absolutely sure that everything was perfect. The makeup made his eyes look huge and the understated shade of lipstick underscored their pouty-ness in a way that Stiles totally approved of. He tugged at some strand of his tousled tomboyish bob wig and finally couldn’t delay any longer to leave the house.

 

Quickly glancing in Derek’s direction, he locked up and took one last moment to just breathe.

 

The older man was again trying to live up to his bad-boy image—sports car, aviator sunglasses and stubble, all check. At least he’d forgone his leather jacket this time. Seriously, was the guy’s image more important than preventing death by heatstroke?

 

Feeling utterly self-conscious as he walked across the lawn, Stiles tried not to check whether his neighbors were out and about. If he couldn’t see them, they wouldn’t be able to see him either. A philosophy he wholeheartedly lived by.

 

He reached the Camaro and got in with a quiet “Hey”, not looking at Derek as he buckled up. The wolf stared at Stiles for a moment from behind his mirrored sunglasses before engaging gear and shooting off in a way that was probably very cool and very law-defying.

 

Stiles had been able to stay superficially calm for the last hour or so, but now his heart broke into a full gallop and his restless hands started tapping out the rhythm of the random pop song that currently came over the speakers.

 

“So,” he started and looked at Derek who didn’t even try to hide a sudden amused grin. Had the wolf just waited for him to give in and fill the silence? Jerk. He decided to let it slide this once because he was seriously anxious over here, okay?

 

“Where are we going?” he asked, undeterred.

 

“Shakin’ Hills,” the wolf rumbled and looked into the side mirror before quickly changing lanes and turning left at the intersection.

 

“You,” Stiles spluttered incredulously, “are taking me out for _milkshakes_?”

 

Derek shrugged and didn’t reply.

 

Shakin’ Hills was a small ice cream parlor at the edge of town that was mainly known for its heavenly milkshakes. It was far enough away from the school district that not many students went there, not even in summer. There were other spots in the center of town that had been established as favorite hangouts, regardless of sub-par taste or tacky interior design. The parlor was as private as it got without leaving Beacon Hills. However, it was still part of the town and Stiles’ dormant panic reared its ugly head. What if they ran into people that recognized him? Stiles didn’t know if he could deal with, well, outing himself.

 

His thoughts a jumbled mess, he stared unseeingly at the passing scenery and couldn’t do anything to calm himself down. He tried to do his breathing exercises without attracting the attention of the werewolf sitting right next to him. As if that was even an option with somebody who could hear your freaking heartbeat.

 

“It’ll be fine,” grumbled Derek all of a sudden, jolting him out of his quickly derailing train of thought.

 

Stiles turned to the wolf with wide eyes.

 

“You know that there’s a reason why I go to _San Francisco_ to run around dressed up like a girl, right?” he said and waved his hands through the air to underscore the gravity of this statement in case Derek didn’t get that this was fucking serious.

 

“I mean, I don’t want to run into people who know who I am, okay? Not only do we have a high-functioning rumor mill, but my dad is the Sheriff! Which is an elective office! The town already thinks I’m a petty criminal, they don’t need to see me in drag on top of that! And what if they decide that this is where their tolerance ends? I’m already dealing with werewolves and hunters and freaking lizard monsters and I can’t deal with plain old bullying on top of that, too,” he was out of breath by the end of his outburst and felt the traitorous sting of tears. Suddenly this outing wasn’t such a good idea after all.

 

Derek glanced at him, totally unimpressed by his tirade.

 

“It’ll be fine,” the wolf repeated and turned his attention back to the road.

 

The rest of the drive was spent in silence and by the time Derek had parked the Camaro and turned off the ignition, Stiles felt almost drugged. It didn’t matter whether he felt up to going out, did it? They were here now so it would be silly to turn back around.

 

Derek stared at him and after a few moments in which Stiles hadn’t moved a muscle, he got the feeling that Derek wanted to say something but was holding back for some reason. Before Stiles could change his mind, he quickly got out of the car. Like ripping off a band-aid, really. He was nervous, yes, unbelievably so in fact, but he knew deep down that he needed to do this. If he chickened out now, he would never be brave enough to spontaneously leave the house in drag again. It would be taking a step backwards, which would obviously not do. He chastised himself for being an idiot (sounding suspiciously like Lydia in his head) and squared his shoulders.

 

Derek got out of the Camaro himself and walked around the car and fell into step beside him. The wolf placed a hand in the small of Stiles’ back and guided him across the street towards the parlor. The gesture was strangely intimate and Stiles felt a tingling sensation all over his body. He couldn’t figure out why Derek was so supportive, so _different_.

 

With every step he took, the heady sensation of being himself grew in intensity. He knew that his legs looked gorgeous in those heels and he reveled in the feeling of the airy dress fluttering around his thighs, the breeze caressing his bare shoulders, the short strands of hair falling haphazardly into his face.

 

He drew his shoulders back, uncurling his slightly hunched-in posture, and took a deep breath. Feeling the air travel freely into his loosened body, his gait became fluent, his balance natural rather than practiced. Stiles loved wearing heals and how they transformed his entire poise. A slow smile tugged on his lips and he turned his face towards the afternoon sun, letting it warm his skin.

 

Derek’s hand guided him securely across uneven cobblestone and into the AC-cooled ice cream parlor. It looked more like a diner, with barstools lining the broad, shiny counter, a polished jukebox on display in one corner and booths furnished with dark turquoise leather.

 

Strangely enough, the parlor wasn’t busy. One booth was occupied by a raucous group of teenagers, another by a couple very much In Love, and there was one solitary guy manning the counter, aggressively decimating a huge bowl of ice cream all by himself.

 

Derek lead him to a booth as far away from the other customers as possible to give them some sort of privacy. Or maybe he was just feeling anti-social today, Stiles didn’t really know. But then, Derek was anti-social most days. If not all days.

 

As soon as they were seated, Stiles crossed his legs in the lady-like way he’d spend hours perfecting in front of the full-length mirror in their guestroom one summer and seized the menu before Derek could even blink. He deserved all the sugar and would order something exorbitant just to make the wolf pay for it. Ignoring his glorified chaperone in favor of scanning the laminated, oversized and horrifyingly colorful menu, Stiles studied every offered variation of ice cream and milk shakes in very great detail—even though he already knew what he wanted anyway. Dragging this out a little was just what he needed: reading about sprinkles and whipped cream and vegan strawberry sundaes dissolved any lingering tension still in his system, and the possibility of annoying Derek in the process was an amusing bonus even though the wolf didn’t seem fazed at all.

 

After a couple of minutes, a waitress arrived at their table, smiling at them in warm welcome. She didn’t react to the fact that Stiles was obviously a guy dressed like a girl. Like at all. There was, in fact, such a distinct lack of judgmental reaction that Stiles briefly wondered whether she was smoking pod on her breaks.

 

Could it really be this easy? His heart rate picked up a notch.

 

Derek’s jeans-clad leg brushed against Stiles’ calf.

 

“What can I get you guys?” asked the perky waitress. Jasmine, her name-tag disclosed to anyone who was interested in that little fact.

 

“Uh, I’ll have the Peanut Butter Fantasy,” Stiles replied, finally putting down the menu.

 

He just couldn’t say no to peanut butter, it was his Kryptonite. Peanut butter and curly fries, really. He would marry the first person who offered an endless supply of both. Seriously, who needed a yacht in the Côte d’Azur or a privet jet when there was peanut butter and curly fries?

 

“Vanilla milkshake,” ordered Derek and Stiles’ head snapped up.

 

The waitress scribbled their order into her little notebook and walked away.

 

“Vanilla? Seriously?” Stiles asked once they were alone and pressed his leg more firmly against Derek’s, feeling ridiculously giddy all of a sudden. “Is that your favorite flavor?”

 

Stiles couldn’t help but stare at the wolf in gleeful delight. How could he possibly swallow the dangerous predator schtick when Derek ordered _vanilla milkshakes_?

 

“Tastes less fake,” the wolf justified sulkily, but the tips of his ears were visibly turning pink.

 

“Uh huh,” Stiles replied and grinned. Sure.

 

They sat in silence for a while and at first, Stiles was strangely reluctant to fill it with random chatter. But after a while he started to fidget, becoming aware of how the straps of his dress dug into his shoulders a little, how his skin felt a bit sticky against the leather bench. He rolled his shoulders and tried to be less conscious about his body, but secretly he only wondered whether he looked silly leaning on his elbows like that. He intertwined his hands in order to stop his fingers from picking up a napkin—he would only fiddle around with it until it came apart—and didn’t notice that his grip tightened and his knuckles turned white.

 

“Stop it,” Derek suddenly interjected in a gruff tone of voice. “You look good.”

 

Stiles glanced at him in surprise. He hadn’t exactly expected to receive any sort of compliment from the man.

 

The thing with Derek was, Stiles decided, that it was hard to get over the first impression you had of him. He still remembered the Derek he’d met a year ago: taciturn, moody, violent. When he had opened his mouth, it was to threaten or to give orders. But if it came right down to it, Derek could be as sassy and eloquent as Stiles if he wanted to. How many times had Stiles witnessed Derek’s dry wit by now? And yet, Stiles’ mental representation of Derek was still hung up on ‘This is private property’ and ‘I’ll rip your throat out. With my teeth’.

 

Maybe it was time to take a second look.

 

“Was there a point to this little outing other than to drag my fabulous ass out of the house?” he finally asked, mostly to conquer the growing awkwardness, but also because he really, really wanted to know.

 

“Sure,” Derek said dryly. “I’ve now lulled you into a false sense of security. Hiding your body will be a piece of cake.”

 

Stiles snorted indelicately.

 

“You say the sweetest things!”

 

Derek shot a quick, wolfish grin at him, full of teeth. But before Stiles had the time to properly enjoy the view, the waitress returned with their order.

 

“Here you go,” she said and smiled at them, putting their desserts carefully on the table between them.

 

“Thanks,” Derek replied and his smile took on that at once brilliant but also entirely fake hue. Stiles felt his heart beat a little faster just knowing that he could recognize Derek’s fake smile where others were completely fooled.

 

Cheeks staining red, the waitress mumbled a quick “enjoy” and hurried back to the counter.

 

Stiles just took a moment to admire the piece of peanut-buttery art in front of him. He took out his phone an took a quick picture. God, he was turning into one of those food porn people, wasn’t he? Just last week he had made a batch of brownies (talk about boredom) and had dicked around on photoshop until it was just right to make his followers on tumblr (the few he had) wanna eat brownies, stat.

 

Then he plunged his spoon into the ice cream and stuffed too much of it into his mouth.

 

“Fuck this is good,” he moaned and ignored his surroundings for a few moments to enjoy his treat.

 

After a while he looked up and nearly chocked to death on whipped cream and sprinkles.

 

The universe was seriously out of line.

 

Derek Hale sucking vanilla milkshake through a straw should be illegal. Like, seriously, he should call the station and report this crime.

 

He tried to look away and failed. Spectacularly.

 

Derek Hale. Was sucking. On a straw.

 

Stiles’ eyes traveled along Derek’s neck in a daze, watching him swallow, then back to his lips wrapped around the plastic straw.

 

Uhm.

 

Maybe this had been a bad idea.

 

It was getting a bit too hot all of a sudden and Stiles was suddenly perfectly aware of his exposed skin, the treacherous blush coloring his cheeks, the less than calm breaths traveling in and out of his body, his nervous heartbeat.

 

Derek suddenly nudged his bare leg with his own jeans-clad one and when Stiles looked up to meet his gaze, there was a knowing little smirk playing on the wolf’s face.

 

Damn.

 

Stiles cleared his throat, spooned ice cream into his mouth and pretended that nothing embarrassing had happened.

 

Denial. His mistress.

 

“So. You mentioned friends in New York,” he asked around the melting sugary peanut-butter-gasm.

 

It was the one thing that he’d been wondering about for a whole month now.

 

“Yes,” the wolf replied.

 

Stiles waited for him to elaborate but he didn’t. Jerk.

 

“And?” he prompted impatiently.

 

“And what?”

 

So this was how they were going to do this?

 

“Are they... crossdressing werewolves?” he asked, because seriously, that would make his day. Year, even.

 

Derek snorted.

 

“No.”

 

Stiles sighed in disappointment. No crossdressing werewolves?

 

“Damn, I would have loved to see that,” he mumbled and spooned some more ice cream into his mouth.

 

“So would they, apparently.”

 

Stiles looked up and frowned.

 

“Huh?”

 

Derek shifted in his seat and for a brief moment he seemed to be a bit uncomfortable.

 

“Well, they always try to make me wear a dress...” Derek admitted gruffly.

 

This time, Stiles did choke on his ice cream and stared at Derek, coughing and wide-eyed, his brain totally on a melt-down.

 

 _Abort, abort. Don’t think about Derek in a dress, don’t think about Derek in a dress_ , he chanted desperately to himself.

 

But alas.

 

Derek. In a dress.

 

It was getting a bit harder to breathe, now.

 

“You’re picturing it right now, aren’t you?” Derek barked, the tips of his ears turning pink in apparent embarrassment.

 

“Well,” Stiles whined. “You can’t drop a bomb like that and _not_ expect me to picture it!”

 

“Shut up,” Derek growled faux-annoyed.

 

Stiles knew that Derek was only embarrassed but he shut up anyway. Derek had been so good about making him feel comfortable that he wanted to return the favor. Although not talking about this was killing him inside. He seriously deserved a medal for his self-restraint.

 

For a while they enjoyed their respective desserts in silence and Derek relaxed in small increments. Not that Stiles was paying attention or anything.

 

Then, he couldn’t take the silence anymore, even though it had been a sort of comfortable one.

 

“Is that why you’re doing this,” Stiles asked and stuffed some more ice cream into his mouth, methodically sucking it off the spoon. Swallowing, he realized that Derek was only staring at him in silence, so he clarified his question. “Because of your crossdressing friends.”

 

Derek hesitated for a brief second.

 

“Not.. entirely,” the wolf replied haltingly. “When Laura and I moved to New York, I was at a bad place. It was hard to.. accept the lupine side of myself, after what had happened.”

 

Stiles didn’t dare blink. Derek had never talked to him about the fire, about Kate, about anything really. Not like this.

 

He sat still like a statue until Derek was ready to continue.

 

“My friends helped me with that,” Derek admitted. “Not all of them are crossdressers, some of them struggled with their sexuality for a long time and... they understood what it meant to have different sides to your personality that are at war with each other, or just not accepted by the general public.”

 

Derek sighed and dragged a hand over his face.

 

“They knew what it means to hide parts of yourself,” the wolf explained. And that made sense, in a way.

 

Stiles nodded and turned back to his Peanut Butter Fantasy.

 

He thought he knew what Derek was trying to tell him. Even though Derek had troubles bearing his soul to others, to him.

 

The wolf knew what he was going through, knew the downsides and offered help in the only way he could. By dragging Stiles out of his comfort zone and showing him ways to integrate both sides of himself into his life.

 

And Stiles was strangely okay with that.

 


End file.
